84186-34-5

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 22755-09-5 N-phenyl hydroxylamine hydrochloride 
• 98-95-3 nitrobenzene 
• 100-65-2 N-Phenylhydroxylamine 
• 19260-03-8 1-(1H-indol-3-yl)-N,N,N-trimethylmethanaminium methyl sulfate 
• 108274-98-2 N-Phenyl-N-skatyl-hydroxylamin 

Downstream Products

• 99763-39-0 (3-indolyl)phenylformamide 
• 99763-43-6 N-acetyl-N-phenyl-3-indolecarboxamide 
• 87959-12-4 ethyl α-ethoxycarbonyl-β-propenoate 
• 99763-40-3 3-phenylaminoindole hydrochloride 
• 87959-01-1 (E)-3-[(1H-Indol-3-yl)-phenyl-amino]-acrylic acid ethyl ester 
• 84186-47-0 ethyl β,β-dipropionate 

Relevant academic research and scientific papers

Indolyl-isoxazolidines attenuate LPS-stimulated pro-inflammatory cytokines and increase survival in a mouse model of sepsis: Identification of potent lead

A library of indolyl-isoxazolidines (6–9) has been synthesized by regio- and stereoselective microwave irradiated 1,3-dipolar cycloadditions of C-(3-indolyl)-N-phenylnitrone (2′) with variedly substituted dipolarophiles (3′-5′) and screened for their anti-inflammatory activities through inhibition of pro-inflammatory cytokines such as TNF-α and IL-6. Amongst the evaluated compounds (6–9), bicyclic isoxazolidine (9a) was found to exhibit significant inhibitory potential against LPS induced human IL-6 and TNF-α in THP-1 cells. Compound 9a was further assessed for in vivo analgesic and anti-inflammatory activities via acetic acid induced writhing and carrageenan induced paw edema models in mice, respectively. The results showed that compound possesses potent anti-inflammatory-analgesic activity comparable to indomethacin and did not show toxicity up to a 2000 mg kg?1 dose as evidenced by histopathological studies. Consequently, the most active compound 9a was also evaluated against LPS-induced septic death and exhibited a significant protection in in vivo mouse model. Taken all together, the results suggest that the compound 9a is able to attenuate pro-inflammatory cytokines such as IL-6 and TNF-α; accelerate resolution of inflammation, and also increased survival rate of septic mice. Therefore, these “lead” isoxazolidines can be used as promising candidate for further analgesic/anti-inflammatory drug design and development.

Investigations on synthesis of indole based constrained mimetic scaffolds through 1,3-dipolar cycloadditions of the C-(3-indolyl)-N-phenylnitrone with a variety of olefinic and allenic dipolarophiles under microwave irradiation

Monomode microwave assisted regio- and stereo-selective 1,3-dipolar cycloadditions of C-(3-indolyl)-N-phenylnitrone (19) with a number of olefinic dipolarophiles (20a-f) afford isoxazolidines (21-26) in high yields, which are conformationally constrained

Formation and reductive ring opening reactions of indolyl bicyclic-isoxazolidines-II:7access to novel natural product analogs

Attempted reductive cleavage of indolyl-bicyclic-isoxazolidines (4a,b; R?=?benzyl, phenyl) with ammonium formate, methanol-THF solvents, at ambient temperature, in the presence of Pd/C lead to facile synthesis of indolyl-α-hydroxy-γ-lactams (5a–b), derive

Copper-Catalyzed Synthesis of Polysubstituted Pyrroles through [3+1+1] Cycloaddition Reaction of Nitrones and Isocyanides

An efficient, copper-catalyzed [3+1+1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting polysubstituted pyrroles from easily available nitrones and α-acidic isocyanides. The given approach features a new mo

Formation and reductive ring opening reactions of indolyl-isoxazolidines: Access to novel natural product analogs and precursors

Regio- and stereoselective 1,3-dipolar cycloadditions of C-(3-indolyl)-N-phenylnitrone (2) with variedly substituted dipolarophiles were carried out to obtain syn- C4 and C5 substituted indolyl-isoxazolidines 6a-c and 7a-f, respectively. Reduction of obtained isoxazolidines, by employing various reducing agents, causes cleavage of the N-O bond, which is accompanied by concomitant cleavage of C-N bond leading to the formation of a library of novel indole based natural product analogs and precursors.

An unexpected catalytic synthesis of novel and known bis(pyrazolyl) methanes by the use of α-aryl-N-phenyl nitrones in aqueous media

Reaction of -aryl-N-phenyl nitrones with 3.methyl-1-phenyl-2-pyrazoline-5-one in the presence of a catalytic amount of silica tungstic acid in EtOH/H2O afforded, unexpectedly, high yields of bis(3-hydroxy-1-phenylpyrazolyl)-arylmethanes instead of the two possible 1,3-addition products. This is the first report of the synthesis of bis(3-hydroxy-1-phenylpyrazolyl)-arylmethanes via the reaction of nitrones and a pyrazolin-5-one. A possible mechanism for the process is suggested.

Reaction of Aldonitrones with Copper Acetylide : Synthesis of Some Novel β-Lactams

Nitrones (7a-e) react with copper acetylide (6) to afford cis- and trans-β-lactams (8 and 9) in good yields.The cis- and trans-isomers have been isolated, respectively as the major and minor products and are characterized through spectral data (IR, mass a

REACTION OF α-3-INDOLYL NITRONES WITH MALONIC ESTERS, INCLUDING MIGRATION OF THE INDOLE RESIDUE

The reaction of α-(3-indolyl) N-aryl(alkyl) nitrones with malonic and methylmalonic esters leads to the formation of derivatives of 3-aminoindole, i.e., the esters of β-N-(3-indolyl)-N-aryl(alkyl)aminopropenoic acids.The reaction was extended to 3-indolyl nitrones differing in the substituents at the nitrogen atom and at position 2 of the indole ring.